Quinacridone derivative, and photoactive layer and photoelectric conversion device including same

ABSTRACT

A quinacridone derivative may be represented by Chemical Formula 1, and a photoactive layer may include the same. A photoelectric conversion device may include a first electrode, a second electrode spaced apart from and configured to face the first electrode, and the photoactive layer including the quinacridone derivative between the first electrode and the second electrode.

PRIORITY STATEMENT

This application claims priority to and the benefit of Korean PatentApplication No. 10-2011-0085898 filed in the Korean IntellectualProperty Office on Aug. 26, 2011, the entire contents of which areincorporated herein by reference.

BACKGROUND

1. Field

Example embodiments recite a quinacridone derivative, and a photoactivelayer and a photoelectric conversion device including the same.

2. Description of the Related Art

Generally, a photoelectric conversion device refers to a device forconverting light into an electrical signal using photoelectric effects.The photoelectric conversion device may have been applied to variousphotosensors, e.g., an automobile sensor, a home sensor, a solar cell,and/or a photodiode. Thereby, research on improving the photoelectricconversion efficiency of a photoelectric conversion device may have beenperformed.

SUMMARY

Example embodiments provide a quinacridone derivative that selectivelyand efficiently absorbs light in a predetermined or given wavelengthrange, and may have improved thermal stability and light absorptionperformance.

Example embodiments also provide a photoactive layer including thequinacridone derivative, and a photoelectric conversion device includingthe photoactive layer.

According to example embodiments, a quinacridone derivative may berepresented by the following Chemical Formula 1.

In Chemical Formula 1,

T¹ to T⁴ may be one of same and different, and each of T¹ to T⁴ may beindependently one of a cyano group (CN), a halogen, a substituted orunsubstituted C₆ to C₃₀ aryl group, and a substituted or unsubstitutedC₂ to C₃₀ heteroaryl group, for example, a cyano group (CN) and ahalogen. X¹ and X² may be one of same and different, and each of X¹ andX² may be independently one of oxygen (O), sulfur (S), and C(CN)₂, forexample, one of oxygen (O) and sulfur (S).

R¹ to R¹⁰ may be one of same and different, and each of R¹ to R¹⁰ areindependently hydrogen, a substituted or unsubstituted C₁ to C₃₀ alkylgroup, a substituted or unsubstituted C₃ to C₃₀ cycloalkyl group, acyano group (CN), a halogen, a substituted or unsubstituted C₆ to C₃₀aryl group, and a substituted or unsubstituted C₂ to C₃₀ heteroarylgroup, for example, one of hydrogen, a substituted or unsubstituted C₁to C₁₀ alkyl group, a substituted or unsubstituted C₃ to C₁₀ cycloalkylgroup, a cyano group (CN), and a halogen.

w1 and w2 may be each independently an integer ranging from 0 to 5, forexample, an integer of 0 or 1. k1 and k2 may be each independently aninteger ranging from 1 to 4, for example, an integer of 1 or 2. n1 andn2 may be each independently an integer ranging from 0 to 3. m1 may bean integer ranging from 1 to 5, for example, an integer ranging from 1to 3.

R¹¹ and R¹² may be one of same and different, and each of R¹¹ and R¹²are independently one of hydrogen, a substituted or unsubstituted C₁ toC₃₀ alkyl group, and a substituted or unsubstituted C₁ to C₃₀ cycloalkylgroup, for example, one of hydrogen, a substituted or unsubstituted C₁to C₁₀ alkyl group, and a substituted or unsubstituted C₃ to C₁₀cycloalkyl group.

The quinacridone derivative may include one selected from compoundsaccording to Chemical Formula 2-1 to Chemical Formulas 2-10, and acombination thereof.

The quinacridone derivative may have a LUMO (lowest unoccupied molecularorbital) level ranging from about −2.0 eV to about −5.0 eV. Thequinacridone derivative may have a bandgap ranging from about 1.5 eV toabout 3.5 eV. The quinacridone derivative may absorb a light in awavelength ranging from about 400 nm to about 700 nm. The quinacridonederivative may have a maximum absorption wavelength ranging from about500 nm to about 600 nm. The quinacridone derivative may have a maximummolar absorption coefficient ranging from about 5.0×10² cm⁻¹·M⁻¹ toabout 1.0×10⁶ cm⁻¹M⁻¹.

According to example embodiments, a photoactive layer may include thequinacridone derivative.

According to example embodiments, a photoelectric conversion device mayinclude a first electrode, a second electrode spaced apart from andconfigured to face the first electrode, and a photoactive layerincluding the quinacridone derivative between the first electrode andthe second electrode.

The photoactive layer may include one selected from a p layer, an ilayer, an n layer, and a combination thereof. When the quinacridonederivative is a p-type material, an n-type material may have a LUMOlevel lower than about −5.0 eV. The quinacridone derivative may beincluded in one selected from the p layer, i layer, and a combinationthereof, and the n-type material may be included in one selected fromthe i layer, n layer, and a combination thereof.

When the quinacridone derivative is an n-type material, a p-typematerial may have a LUMO level higher than −2.0 eV. The quinacridonederivative may be included in one selected from the i layer, n layer,and a combination thereof, and the p-type material may be included inone selected from the p layer, i layer, and a combination thereof.

The photoelectric conversion device may be a photodiode, a solar cell, aphotovoltaic cell, an image sensing device, a photodetector, aphotosensor, or an organic light emitting diode (OLED).

BRIEF DESCRIPTION OF THE DRAWINGS

Example embodiments will be more clearly understood from the followingdetailed description taken in conjunction with the accompanyingdrawings. FIGS. 1-4 represent non-limiting, example embodiments asdescribed herein

FIG. 1 is the schematic cross-sectional view of a photoelectricconversion device according to example embodiments.

FIG. 2 shows a ¹H NMR spectrum of the quinacridone derivative accordingto Example 1.

FIG. 3 shows a ¹³C NMR spectrum of the quinacridone derivative accordingto Example 1.

FIG. 4 shows ultraviolet visible ray (UV-Vis) absorption spectra of thequinacridone derivatives according to Example 1 and Comparative Example1.

It should be noted that these Figures are intended to illustrate thegeneral characteristics of methods, structure and/or materials utilizedin certain example embodiments and to supplement the written descriptionprovided below. These drawings are not, however, to scale and may notprecisely reflect the precise structural or performance characteristicsof any given embodiment, and should not be interpreted as defining orlimiting the range of values or properties encompassed by exampleembodiments. For example, the relative thicknesses and positioning ofmolecules, layers, regions and/or structural elements may be reduced orexaggerated for clarity. The use of similar or identical referencenumbers in the various drawings is intended to indicate the presence ofa similar or identical element or feature.

DETAILED DESCRIPTION

It will be understood that when an element is referred to as being“connected” or “coupled” to another element, it can be directlyconnected or coupled to the other element or intervening elements may bepresent. In contrast, when an element is referred to as being “directlyconnected” or “directly coupled” to another element, there are nointervening elements present. Like numbers indicate like elementsthroughout. As used herein the term “and/or” includes any and allcombinations of one or more of the associated listed items.

It will be understood that, although the terms “first”, “second”, etc.may be used herein to describe various elements, components, regions,layers and/or sections, these elements, components, regions, layersand/or sections should not be limited by these terms. These terms areonly used to distinguish one element, component, region, layer orsection from another element, component, region, layer or section. Thus,a first element, component, region, layer or section discussed belowcould be termed a second element, component, region, layer or sectionwithout departing from the teachings of example embodiments.

Spatially relative terms, such as “beneath,” “below,” “lower,” “above,”“upper” and the like, may be used herein for ease of description todescribe one element or feature's relationship to another element(s) orfeature(s) as illustrated in the figures. It will be understood that thespatially relative terms are intended to encompass differentorientations of the device in use or operation in addition to theorientation depicted in the figures. For example, if the device in thefigures is turned over, elements described as “below” or “beneath” otherelements or features would then be oriented “above” the other elementsor features. Thus, the exemplary term “below” can encompass both anorientation of above and below. The device may be otherwise oriented(rotated 90 degrees or at other orientations) and the spatially relativedescriptors used herein interpreted accordingly.

The terminology used herein is for the purpose of describing particularembodiments only and is not intended to be limiting of exampleembodiments. As used herein, the singular forms “a,” “an” and “the” areintended to include the plural forms as well, unless the context clearlyindicates otherwise. It will be further understood that the terms“comprises”, “comprising”, “includes” and/or “including,” if usedherein, specify the presence of stated features, integers, steps,operations, elements, and/or components, but do not preclude thepresence or addition of one or more other features, integers, steps,operations, elements, components, and/or groups thereof.

Example embodiments are described herein with reference tocross-sectional illustrations that are schematic illustrations ofidealized embodiments (and intermediate structures) of exampleembodiments. As such, variations from the shapes of the illustrations asa result, for example, of manufacturing techniques and/or tolerances,are to be expected. Thus, example embodiments should not be construed aslimited to the particular shapes of regions illustrated herein but areto include deviations in shapes that result, for example, frommanufacturing. For example, an implanted region illustrated as arectangle will, typically, have rounded or curved features and/or agradient of implant concentration at its edges rather than a binarychange from implanted to non-implanted region. Likewise, a buried regionformed by implantation may result in some implantation in the regionbetween the buried region and the surface through which the implantationtakes place. Thus, the regions illustrated in the figures are schematicin nature and their shapes are not intended to illustrate the actualshape of a region of a device and are not intended to limit the scope ofexample embodiments.

Unless otherwise defined, all terms (including technical and scientificterms) used herein have the same meaning as commonly understood by oneof ordinary skill in the art to which example embodiments belong. Itwill be further understood that terms, such as those defined incommonly-used dictionaries, should be interpreted as having a meaningthat is consistent with their meaning in the context of the relevant artand will not be interpreted in an idealized or overly formal senseunless expressly so defined herein.

As used herein, when a specific definition is not otherwise provided,the term “substituted” refers to one substituted with at least onesubstituent selected from one of a halogen (—F, —Cl, —Br, or —I), ahydroxy group, a nitro group, a cyano group, an amino group (NH₂,NH(R²⁰⁰), or N(R²⁰¹)(R²⁰²), wherein R²⁰⁰, R²⁰¹, and R²⁰² may be one ofsame and different, and each of R²⁰⁰, R²⁰¹, and R²⁰² may beindependently one of a C₁ to C₁₀ alkyl group), an adidino group, ahydrazine group, a hydrazone group, a carboxyl group, a substituted orunsubstituted alkyl group, a substituted or unsubstituted haloalkylgroup, a substituted or unsubstituted alkoxy group, a substituted orunsubstituted alkenyl group, a substituted or unsubstituted alkynylgroup, a substituted or unsubstituted aryl group, a substituted orunsubstituted heteroaryl group, and a substituted or unsubstitutedheterocycloalkyl group in place of at least one hydrogen of a functionalgroup.

As used herein, when a specific definition is not otherwise provided,the term “alkyl group” may refer to a C₁ to C₃₀ alkyl group,specifically a C₁ to C₂₀ alkyl group, and more specifically a C₁ to C₁₀alkyl group, the term “cycloalkyl group” may refer to a C₃ to C₃₀cycloalkyl group, specifically a C₃ to C₂₀ cycloalkyl group, and morespecifically a C₃ to C₁₀ cycloalkyl group, the term “alkenyl group” mayrefer to a C₂ to C₃₀ alkenyl group, specifically a C₂ to C₂₀ alkenylgroup, and more specifically a C₂ to C₁₀ alkenyl group, the term“alkynyl group” may refer to a C₂ to C₃₀ alkynyl group, specifically aC₂ to C₂₀ alkynyl group, and more specifically a C₂ to C₁₀ alkynylgroup, the term “alkoxy group” may refer to a C₁ to C₃₀ alkoxy group,specifically a C₁ to C₂₀ alkoxy group, and more specifically a C₁ to C₁₀alkoxy group, the term “aryl group” may refer to a C₆ to C₃₀ aryl group,specifically a C₆ to C₂₀ aryl group, and more specifically a C₆ to C₁₅aryl group, the term “heteroaryl group” may refer to a C₂ to C₃₀heteroaryl group, specifically a C₂ to C₂₀ heteroaryl group, and morespecifically a C₂ to C₁₅ heteroaryl group, the term “heterocycloalkylgroup” may refer to a C₂ to C₃₀ heterocycloalkyl group, specifically aC₂ to C₂₀ heterocycloalkyl group, and more specifically a C₂ to C₁₅heterocycloalkyl group, and the term “halogen” may refer to F, Cl, Br,or I.

As used herein, when a definition is not otherwise provided, the terms“heterocycloalkyl group” and “heteroaryl group” may independently referto a cycloalkyl group and an aryl group including one to threeheteroatoms of N, O, S, Si, or P and the remainder being carbon in onecyclic structure.

As used herein, when a definition is not otherwise provided,“combination” generally refers to mixing or copolymerization. As usedherein, when a definition is not otherwise provided, the term“copolymerization” refers to block copolymerization, randomcopolymerization, or graft copolymerization, and the term “copolymer”refers to a block copolymer, a random copolymer, or a graft copolymer.

As used herein, when a definition is not otherwise provided in thespecification, “i layer” is made of a mixture of a p-type material andan n-type material and forms a PN junction, and plays a role ofreceiving light, producing excitons, and separating the excitons intoholes and electrons. Herein, the p-type material may be the same as ordifferent from a material forming a p layer. The n-type material may bethe same as or different from a material forming an n layer. The “player” may include a p-type material, and the holes separated fromexcitons produced may be transported thereto. The “n layer” may includean n-type material, and the electrons separated from excitons producedmay be transported thereto.

In the drawings, the thickness of layers, films, panels, regions, etc.,may be exaggerated for clarity. Like reference numerals designate likeelements throughout the specification. It will be understood that whenan element such as a layer, film, or substrate is referred to as being“on” another element, it can be directly on the other element orintervening elements may also be present.

According to example embodiments, a quinacridone derivative may berepresented by the following Chemical Formula 1.

In Chemical Formula 1, T¹ to T⁴ may be one of same and different, andeach of T¹ to T⁴ may be independently one of a cyano group (CN), ahalogen, a substituted or unsubstituted C₆ to C₃₀ aryl group, and asubstituted or unsubstituted C₂ to C₃₀ heteroaryl group, for example,one of a cyano group (CN) and a halogen, e.g., a cyano group (CN). X¹and X² may be one of same and different, and each of X¹ and X² may beindependently one of oxygen (O), sulfur (S), and C(CN)₂, for example,one of oxygen (O) and sulfur (S), e.g., oxygen (O).

R¹ to R¹⁰ may be one of same and different, and each of R¹ to R¹⁰ may beindependently one of hydrogen, a substituted or unsubstituted C₁ to C₃₀alkyl group, a substituted or unsubstituted C₃ to C₃₀ cycloalkyl group,a cyano group (CN), a halogen, a substituted or unsubstituted C₆ to C₃₀aryl group, and a substituted or unsubstituted C₂ to C₃₀ heteroarylgroup, for example, one of hydrogen, a substituted or unsubstituted C₁to C₁₀ alkyl group, a substituted or unsubstituted C₃ to C₁₀ cycloalkylgroup, a cyano group (CN), and a halogen, e.g., one of hydrogen, asubstituted or unsubstituted C₁ to C₅ alkyl group, and a cyano group(CN).

w1 and w2 may be each independently an integer ranging from 0 to 5, forexample, an integer of 0 or 1, e.g., 0. k1 and k2 may be eachindependently an integer ranging from 1 to 4, for example, an integer of1 or 2, e.g., 1. n1 and n2 may be each independently an integer rangingfrom 0 to 3. m1 is an integer ranging from 1 to 5, for example, aninteger ranging from 1 to 3, e.g., an integer of 1 or 2.

R¹¹ and R¹² may be one of same and different, and each of R¹¹ and R¹²may be independently one of hydrogen, a substituted or unsubstituted C₁to C₃₀ alkyl group, and a substituted or unsubstituted C₃ to C₃₀cycloalkyl group, for example, one of hydrogen, a substituted orunsubstituted C₁ to C₁₀ alkyl group, and a substituted or unsubstitutedC₃ to C₁₀ cycloalkyl group, e.g., one of hydrogen and a substituted orunsubstituted C₁ to C₅ alkyl group.

The quinacridone derivative represented by the above Chemical Formula 1may include an electron accepting functional group at both ends of amain chain and an electron donating functional group at the center ofthe main chain. Because the quinacridone derivative may include both theelectron accepting functional group and the electron donating functionalgroup in a molecule, the quinacridone derivative may increase aphoto-transition dipole moment, and thus, have a higher light absorptioncoefficient.

In addition, because the quinacridone derivative represented by theabove Chemical Formula 1 may include an electron accepting functionalgroup at both ends of a main chain, the electron accepting functionalgroup may decrease LUMO (lowest unoccupied molecular orbital) and HOMO(highest occupied molecular orbital) levels of the quinacridonederivative, in other words, the electron accepting functional group mayincrease the electron volt (eV) absolute value, and decrease the bandgapof the quinacridone derivative. Accordingly, the quinacridone derivativemay effectively absorb light in a visible ray region, for example, in aregion of about 400 nm to about 700 nm, e.g., in a region of about 500nm to about 600 nm, and may have higher external quantum efficiency(EQE), thereby effectively improving photoelectric conversionefficiency.

Particularly, the quinacridone derivative according to the aboveChemical Formula 1 may include one selected from compounds according toChemical Formula 2-1 to Chemical Formulas 2-10, and a combinationthereof, but is not limited thereto.

The quinacridone derivative may have a LUMO level ranging from about−2.0 eV to about −5.0 eV. When the quinacridone derivative has a LUMOlevel within the range, the quinacridone derivative may have higherexternal quantum efficiency (EQE), and thus, effectively improvephotoelectric conversion efficiency, and may be included in one selectedfrom a p layer, an i layer, an n layer, and a combination thereof. Forexample, the quinacridone derivative may have a LUMO level ranging fromabout −3.0 eV to about −4.6 eV, e.g., from about −3.4 eV to about −4.6eV.

The quinacridone derivative may have a bandgap ranging from about 1.5 eVto about 3.5 eV. When the quinacridone derivative has a bandgap withinthe range, the quinacridone derivative may effectively absorb light in avisible ray region, for example, in a region ranging from about 400 nmto about 700 nm, e.g., in a region of about 500 nm to about 600 nm, andmay have a selective photoelectric conversion characteristic for greenlight in the visible ray region. For example, the quinacridonederivative may have a bandgap ranging from about 1.7 eV to about 3.1 eV,e.g., from about 2.0 eV to about 2.5 eV.

The quinacridone derivative may absorb light in a wavelength regionranging from about 400 nm to about 700 nm and may have a maximumabsorption wavelength ranging from about 500 nm to about 600 nm.Accordingly, the quinacridone derivative may effectively absorb lightwith a particular wavelength range in a visible ray region, and thus mayhave a photoelectric conversion characteristic for light in a particularwavelength range due to absorption wavelength selectivity andphotoelectric conversion selectivity, thereby effectively improvingphotoelectric conversion efficiency.

The quinacridone derivative may have a maximum molar absorptioncoefficient ranging from about 5.0×10² cm⁻¹·M⁻¹ to about 1.0×10⁶cm⁻¹·M⁻¹. Accordingly, the quinacridone derivative may effectivelyabsorb light in a particular wavelength range and improve photoelectricconversion efficiency. In particular, the quinacridone derivative mayhave a maximum molar absorption coefficient ranging from about 1.0×10⁴cm⁻¹·M⁻¹ to about 1.0×10⁶ cm⁻¹·M⁻¹, for example, about 4.0×10⁴ cm⁻¹·M⁻¹to about 1.0×10⁵ cm⁻¹·M⁻¹.

According to example embodiments, a photoactive layer may include thequinacridone derivative.

According to example embodiments, a photoelectric conversion device mayinclude a first electrode, a second electrode spaced apart from andconfigured to face the first electrode, and a photoactive layer thatincludes the quinacridone derivative between the first and secondelectrodes.

Hereinafter, a photoactive layer and a photoelectric conversion deviceaccording to example embodiments are illustrated referring to FIG. 1.

FIG. 1 is, a schematic cross-sectional view of a photoelectricconversion device according to example embodiments. Hereinafter, forbetter understanding and ease of description, the light-receivingsurface of a photoactive layer 130 that receives light may be referredto as a front side, and the opposite side may be referred to as a rearside.

Referring to FIG. 1, a photoelectric conversion device 100 according toexample embodiments may include a front electrode 150 and a rearelectrode 110 spaced apart by a predetermined or given interval andfacing each other, and a photoactive layer 130 disposed between the rearelectrode 110 and the front electrode 150.

The rear electrode 110 may include a metal or a transparent conductivematerial. The metal may include one selected from Al, Cu, Ti, Au, Pt,Ag, Cr, Li, and a combination thereof, the transparent conductivematerial may include one selected from ITO (indium tin oxide),indium-doped ZnO (IZO), aluminum-doped ZnO (AZO), gallium-doped ZnO(GZO), antimony-doped tin oxide (ATO), fluorine-doped tin oxide (FTO),tin oxide (SnO₂), ZnO, and a combination thereof, but are not limitedthereto.

When the rear electrode 110 may include a metal, the rear electrode 110may be formed as a semitransparent electrode with a thickness equal toor less than about 20 nm, but is not limited thereto.

The front electrode 150 may include a transparent conductive material.Unless mentioned otherwise, the transparent conductive material may bethe same as described above.

The front electrode 150 may have an equal or higher work function thanthe rear electrode 110, but is not limited thereto. When the frontelectrode 150 has a higher work function than the rear electrode 110,electrons separated from excitons obtained from the photoactive layer130 may be collected into the rear electrode 110, and holes separatedfrom the excitons may be collected into the front electrode 150.

The photoactive layer 130 may convert light into electrical signalsusing the photoelectric effect, and may include the quinacridonederivative represented by the above Chemical Formula 1.

The photoactive layer 130 may include one selected from a p layer, an ilayer, an n layer, and a combination thereof. The photoactive layer 130may convert light into an electrical signal using photoelectric effects.

The p layer may contact the front electrode 150, the n layer may contactthe rear electrode 110, and the i layer may contact one selected fromthe p layer, the n layer, and a combination thereof. However, exampleembodiments are not limited thereto. The p layer and the n layer may notbe formed, and the i layer may contact the front electrode 150 and therear electrode 110.

Herein, the quinacridone derivative may be included in one selected fromthe p layer, the i layer, the n layer, and a combination thereof.

For example, when the quinacridone derivative is a p-type material, ann-type material may have a lower LUMO level than the quinacridonederivative, for example, a larger electron volt (eV) absolute value.Herein, the quinacridone derivative may be included in one selected fromthe p layer, the i layer, and a combination thereof, and the n-typematerial may be included in one selected from the i layer, the n layer,and a combination thereof, which may form a photoactive layer 130.

As another example, when the quinacridone derivative is an n-typematerial, a p-type material may have a higher LUMO level than thequinacridone derivative, for example, a smaller electron volt (eV)absolute value. Herein, the quinacridone derivative may be included inone selected from the i layer, the n layer, and a combination thereof,and the p-type material may be included in one selected from the player, the i layer, and a combination thereof, which may form aphotoactive layer 130.

The i layer may include one selected from a bulk heterojunction (BHJ),an organic/inorganic hybrid layer, and a combination thereof, but is notlimited thereto.

The bulk heterojunction may include at least two selected from thequinacridone derivative according to the above Chemical Formula 1,polyaniline, polypyrrole, polythiophene, poly(p-phenylene-vinylene),poly(2-methoxy-5-(2′-ethyl-hexyloxy)-1,4-phenylene-vinylene) (MEH-PPV),poly(2-methoxy-5-(3,7-dimethyloctyloxy)-1,4-phenylene-vinylene)(MDMO-PPV), pentacene, poly(3,4-ethylene-dioxythiophene) (PEDOT),poly(3-alkylthiophene), phthalocyanine, triarylamine, benzidine,pyrazoline, styrylamine, hydrazone, carbazole, thiophene, pyrrole,phenanthrene, tetracene, naphthalene, fullerene (C60, C70, C74, C76,C78, C82, C84, C720, and C860),1-(3-methoxy-carbonyl)propyl-1-phenyl(6,6)C61 (PCBM), C71-PCBM,C84-PCBM, bis-PCBM, perylene, derivatives thereof, and combinationsthereof, but are not limited thereto.

When using materials having different energy levels from each other whenproviding a bulk heterojunction, a material having a relatively low LUMOlevel may be used for an n-type material, and a material having arelatively high LUMO level may be used for a p-type material.

The organic/inorganic hybrid layer may include an organic materialselected from the quinacridone derivative represented by the aboveChemical Formula 1, polyaniline, polypyrrole, polythiophene,poly(p-phenylene-vinylene),poly[2-methoxy-5-(2′-ethyl-hexyloxy)-1,4-phenylene-vinylene) (MEH-PPV),poly(2-methoxy-5-(3,7-dimethyloctyloxy)-1,4-phenylene-vinylene)(MDMO-PPV), pentacene, poly(3,4-ethylene-dioxythiophene) (PEDOT),poly(3-alkylthiophene), phthalocyanine, triarylamine, benzidine,pyrazoline, styrylamine, hydrazone, carbazole, thiophene, pyrrole,phenanthrene, tetracene, naphthalene, fullerene (C60, C70, C74, C76,C78, C82, C84, C720, and C860),1-(3-methoxy-carbonyl)propyl-1-phenyl(6,6)C61 (PCBM), C71-PCBM,C84-PCBM, bis-PCBM, perylene, a derivative thereof, and a combinationthereof, but is not limited thereto, and an inorganic semiconductorselected from CdS, CdTe, CdSe, ZnO, and combinations thereof, but is notlimited thereto. When using materials having different energy levelsfrom each other when providing an organic/inorganic hybrid layer, amaterial having a relatively low LUMO (lowest unoccupied molecularorbital) level may be used for an n-type material, and a material havingrelatively high LUMO level may be used for a p-type material.

When the i layer with the p layer and the n layer and a combinationthereof forms a photoactive layer, a material for the p layer may be ap-type material used for the i layer, and a material for the n layer maybe an n-type material for the i layer. However, example embodiments arenot limited thereto, a p-type material for the i layer may differ from ap-type material for the p layer, and an n-type material for the i layermay differ from an n-type material for the n layer.

For example, when a material for the p layer is a p-type material forthe i layer, and a material for the n layer is a n-type material for thei layer, the p and i layers may have lower interface resistance, therebytransporting holes faster and improving photoelectric conversionefficiency. In addition, the i and n layers may have lower interfaceresistance, thereby transporting electrons faster and improvingphotoelectric conversion efficiency.

The p layer and n layer may include a photoactive material that may beselected from the quinacridone derivative according to the aboveChemical Formula 1, polyaniline, polypyrrole, polythiophene,poly(p-phenylene-vinylene),poly(2-methoxy-5-(2′-ethyl-hexyloxy)-1,4-phenylene-vinylene) (MEH-PPV),poly(2-methoxy-5-(3,7-dimethyloctyloxy)-1,4-phenylene-vinylene)(MDMO-PPV), pentacene, poly(3,4-ethylene-dioxythiophene) (PEDOT),poly(3-alkylthiophene), phthalocyanine, triarylamine, benzidine,pyrazoline, styrylamine, hydrazone, carbazole, thiophene, pyrrole,phenanthrene, tetracene, naphthalene, fullerene (C60, C70, C74, C76,C78, C82, C84, C720, and C860),1-(3-methoxy-carbonyl)propyl-1-phenyl(6,6)C61 (PCBM), C71-PCBM,C84-PCBM, bis-PCBM, perylene, CdS, CdTe, CdSe, ZnO, derivatives thereof,and combinations thereof, but is not limited thereto.

When the photoactive layer may include both the p and n layers, amaterial with a relatively lower LUMO level among the photoactivematerials may form an n layer, while a material with a relatively higherLUMO level among the photoactive materials may form a p layer.

The photoactive layer 130 may have a thickness of about 10 nm to about200 nm. When the photoactive layer 130 has a thickness within theaforementioned range, the photoactive layer 130 may effectively absorblight to be converted into electricity, effectively separate theexcitons into holes and electrons, and effectively transfer the holesand electrons separated from excitons, so as to effectively improve thephotoelectric conversion efficiency. For example, the photoactive layer130 may have a thickness of about 10 nm to about 100 nm.

Although not shown in FIG. 1, one selected from an electron transportlayer (ETL), a hole blocking layer (HBL), and a combination thereof maybe formed between the rear electrode 110 and the photoactive layer 130,and one selected from a hole transport layer (HTL), an electron blockinglayer (EBL), and a combination thereof may be formed between the frontelectrode 150 and the photoactive layer 130.

The electron transport layer (ETL) may play a role of facilitating thetransport of electrons, and may include one selected from1,4,5,8-naphthalene-tetracarboxylic dianhydride (NTCDA), bathocuproine(BCP), LiF, Alq₃, Gaq₃, Inq₃, Znq₂, Zn(BTZ)₂, BeBq₂, and a combinationthereof, but is not limited thereto.

The hole blocking layer (HBL) may play a role of prohibiting thetransport of holes and simultaneously play a role of a protective layerfor preventing or inhibiting an electrical short, and may include oneselected from 1,4,5,8-naphthalene-tetracarboxylic dianhydride (NTCDA),bathocuproine (BCP), LiF, Alq₃, Gaq₃, Inq₃, Znq₂, Zn(BTZ)₂, BeBq₂, and acombination thereof, but is not limited thereto.

The hole transporting layer (HTL) may play a role of facilitating thetransport of holes, and may include one selected frompoly(3,4-ethylene-dioxythiophene):poly(styrene-sulfonate) (PEDOT:PSS),polyarylamine, poly(N-vinylcarbazole), polyaniline, polypyrrole,N,N,N′,N′-tetrakis(4-methoxyphenyl)-benzidine (TPD),4-bis[N-(1-naphthyl)-N-phenyl-amino]biphenyl (α-NPD),4,4′,4″-tris(N-3-methylphenyl-N-phenylamino)triphenylamine (m-MTDATA),4,4′,4″-tris(N-carbazolyl)-triphenylamine (TCTA), and a combinationthereof, but is not limited thereto.

The electron blocking layer (EBL) may play a role of prohibiting thetransport of electrons, and may include one selected frompoly(3,4-ethylene-dioxythiophene):poly(styrene-sulfonate) (PEDOT:PSS),polyarylamine, poly(N-vinylcarbazole), polyaniline, polypyrrole,N,N,N′,N′-tetrakis(4-methoxyphenyl)-benzidine (TPD),4-bis[N-(1-naphthyl)-N-phenyl-amino]biphenyl (α-NPD),4,4′,4″-tris(N-3-methylphenyl-N-phenylamino)triphenylamine (m-MTDATA),4,4′,4″-tris(N-carbazolyl)-triphenylamine (TCTA), and a combinationthereof, but is not limited thereto.

Accordingly, the photoelectric conversion device including a photoactivelayer including the quinacridone derivative may be a photodiode, a solarcell (or a photovoltaic cell), an image sensing device, a photodetector,a photosensor, or an organic light emitting diode (OLED), but is notlimited thereto.

EXAMPLES

The following examples illustrate this disclosure in more detail.However, example embodiments are not limited thereto.

Example 1 Preparation of Quinacridone Derivative

A quinacridone derivative is prepared according to the followingReaction Scheme 1.

First Step: Synthesis of N,N′-dimethylquinacridone

30 ml of toluene is placed into a 100 ml round-bottomed flask, and 1mmol of quinacridone and 4 mmol of tetrabutylammonium iodide are addedthereto and dissolved therein. While the solution is fervently agitated,1 ml of 50% NaOH and 2.4 mmol of 1-iodomethane are slowly added thereto.

The mixture is refluxed and heated for about 26 hours. 10 ml of water isused to complete the reaction, and the reactant is filtrated. Throughthe filtration, an organic layer is separated, and a solvent is removedunder reduced pressure.

The obtained crude product is dissolved in dichloromethane, and thesolution is purified through column chromatography, preparingN,N′-dimethylquinacridone. Herein, the yield is 25%.

¹H NMR (600 MHz, CDCl₃) Calcd.: δH 7.56 (d, 2H), 7.42 (m, 2H), 6.87 (m,2H), 6.70 (d, 2H), 6.69 (s, 2H), 3.20 (s, 6H)

MS: m/z 340.12 (100.0%), 341.12 (24.5%), 342.13 (3.2%)

Chemical Formula: C₂₂H₁₆N₂O₂.

Anal. Calcd.: C, 77.63; H, 4.74; N, 8.23; O, 9.40.

Second Step: Synthesis of N,N′-dimethyl-2,9-diformylquinacridone

2 mmol of phosphorus oxychloride is added to 4 mmol of agitatedN,N-dimethylformamide (DMF) at 0° C. in a dropwise fashion. The mixtureis agitated at 0° C. for 1 hour and further agitated at room temperaturefor 1 hour.

1 mmol of N,N′-dimethylquinacridone dissolved in dichloroethane is addedto the reactant. The mixture is agitated at 90° C. for 2 hours. Theagitated reactant is cooled down and poured into cold water. The mixtureis neutralized to have a pH of 7 using a 2 N NaOH aqueous solution andextracted with dichloromethane.

The extract is washed with a large amount of a saline solution, and itssolvent is removed under reduced pressure. The residue is purifiedthrough silica gel column chromatography using dichloromethane/n-hexanemixed in a volume ratio of 5/1, preparingN,N′-dimethyl-2,9-diformylquinacridone. Herein, the yield is 53%.

¹H NMR (600 MHz, CDCl₃) Calcd.: δH 9.88 (s, 2H), 7.37 (s, 2H), 7.29 (d,2H), 6.89 (d, 2H), 6.69 (s, 2H), 3.20 (s, 6H)

MS: m/z 396.11 (100.0%), 397.11 (26.7%), 398.12 (4.1%)

Chemical Formula: C₂₄H₁₅N₂O₄.

Anal. Calcd.: C, 72.72; H, 4.07; N, 7.07; O, 16.14.

Third Step: Synthesis ofN,N′-dimethyl-2,9-bis(dicyanoethenyl)quinacridone

A mixture of 1 mmol of N,N′-dimethyl-2,9-diformylquinacridone and 2 mmolof malononitrile is added to 10 ml of ethanol, and Ni nanoparticles(diameter ranging from 15 nm to 20 nm, 10 mol %) as a catalyst are addedthereto.

The mixture is agitated at room temperature for 30 minutes, diluted with10 ml of dichloromethane, and washed with water three times and with asaline solution. An obtained organic layer is dried under anhydroussodium sulfate (Na₂SO₄), and the solvent therein is removed underreduced pressure using a rotary evaporator.

The resulting reactant is recrystallized with ethyl acetate, preparingN,N′-dimethyl-2,9-bis(dicyanoethenyl)quinacridone represented by thefollowing Chemical Formula 2-1, which is a red crystalline powder.Herein, the yield is 93%.

¹H NMR (600 MHz, CDCl₃) Calcd.: δH 7.87 (d, 2H), 7.79 (s, 2H), 6.86 (s,2H), 6.65 (d, 2H), 6.69 (s, 2H), 3.20 (s, 6H)

MS: m/z 492.13 (100.0%), 493.14 (32.7%), 494.14 (5.6%), 493.13 (2.2%)

Chemical Formula: C₃₀H₁₆N₆O₂.

Anal. Calcd.: C, 73.16; H, 3.27; N, 17.06; O, 6.50.

Comparative Example 1 Quinacridone Derivative

A compound according to the following Chemical Formula 3 is used as aquinacridone derivative.

Experimental Example 2 NMR Measurement

The quinacridone derivative according to Example 1 is analyzed regarding¹H NMR and ¹³C NMR. The results are respectively provided in FIGS. 2 and3.

FIG. 2 shows peaks in the following Chemical Formula 4, identifying thequinacridone derivative according to Example 1 to be a resultingmaterial according to Reaction Scheme 1.

In addition, FIG. 3 shows peaks in the following Chemical Formula 5,identifying the quinacridone derivative of Example 1 to be a resultingmaterial according to Reaction Scheme 1.

Experimental Example 2 Bandgap Measurement

The quinacridone derivatives according to Example 1 and ComparativeExample 1 are respectively measured regarding HOMO and LUMO levels andbandgap in a cyclic voltammetry (CV) method. The results are provided inthe following Table 1.

TABLE 1 HOMO (eV) LUMO (eV) Bandgap (eV) Example 1 −6.16 −3.17 2.99Comparative −5.25 −2.13 3.12 Example 1

As shown in Table 1, the quinacridone derivative of Example 1 may have asmaller bandgap than the quinacridone derivative of Comparative Example1.

Experimental Example 3 Light Absorption Characteristic Evaluation

The quinacridone derivatives according to Example 1 and ComparativeExample 1 are respectively dissolved in dichlorobenzene, and eachsolution is dripped on a glass plate. The solutions are dried to removea solvent therein, obtaining films. The films are evaluated regardingeach ultraviolet visible ray (UV-Vis) absorption spectrum using Cary5000 UV spectroscopy equipment made by Varian, Inc.

The results are provided in FIG. 4. As shown in FIG. 4, the quinacridonederivative of Example 1 may have maximum absorption wavelengths of about520 nm and about 580 nm, and a maximum molar absorption coefficient ofabout 1.0×10⁵ cm⁻¹·M⁻¹. In addition, the quinacridone derivative ofExample 1 sufficiently absorbs light in a wavelength region ranging fromabout 450 nm to about 650 nm.

On the other hand, the quinacridone derivative of Comparative Example 1may have a maximum molar absorption coefficient of about 1.0×10⁴cm⁻¹·M⁻¹, and partly absorbs light in a wavelength region ranging fromabout 500 nm to about 600 nm. Resultantly, the quinacridone derivativeof Example 1 may have a relatively small bandgap and an improved lightabsorption characteristic.

While this disclosure has been described in connection with what ispresently considered to be example embodiments, it is to be understoodthat the inventive concepts are not limited to the disclosedembodiments, but, on the contrary, is intended to cover variousmodifications and equivalent arrangements included within the spirit andscope of the appended claims.

What is claimed is:
 1. A photoelectric conversion device, comprising: afirst electrode; a second electrode spaced apart from and configured toface the first electrode; and a photoactive layer between the firstelectrode and the second electrode, the photoactive layer including aquinacridone derivative represented by Chemical Formula 1:

wherein, in Chemical Formula 1, T¹ to T⁴ are one of same and different,and each of T¹ to T⁴ are independently one of a cyano group (CN), ahalogen, a substituted or unsubstituted C₆ to C₃₀ aryl group, and asubstituted or unsubstituted C₂ to C₃₀ heteroaryl group, X¹ and X² areone of same and different, and each of X¹ and X² are independently oneof oxygen (O), sulfur (S), and C(CN)₂, R¹ to R¹⁰ are one of same anddifferent, and each of R¹ to R¹⁰ are independently one of hydrogen, asubstituted or unsubstituted C₁ to C₃₀ alkyl group, a substituted orunsubstituted C₃ to C₃₀ cycloalkyl group, a cyano group (CN), a halogen,a substituted or unsubstituted C₆ to C₃₀ aryl group, and a substitutedor unsubstituted C₂ to C₃₀ heteroaryl group, wherein at least one of R¹and R² is not hydrogen, w1 and w2 are each independently an integerranging from 0 to 5, k1 and k2 are each independently an integer rangingfrom 1 to 4, n1 and n2 are each independently an integer ranging from 0to 3, m1 is an integer ranging from 1 to 5, and R¹¹ and R¹² are one ofsame and different, and each of R¹¹ and R¹² are independently one ofhydrogen, a substituted or unsubstituted C₁ to C₃₀ alkyl group, and asubstituted or unsubstituted C₃ to C₃₀ cycloalkyl group.
 2. Thephotoelectric conversion device of claim 1, wherein the photoactivelayer includes one selected from a p layer, an i layer, an n layer, anda combination thereof.
 3. The photoelectric conversion device of claim2, wherein the quinacridone derivative is a p-type material, and amaterial with a LUMO level lower than about −5.0 eV is an n-typematerial, and the quinacridone derivative is included in one selectedfrom the p layer, the i layer, and a combination thereof, and the n-typematerial is included in one selected from the i layer, the n layer, anda combination thereof.
 4. The photoelectric conversion device of claim2, wherein the quinacridone derivative is an n-type material, and amaterial with a LUMO level higher than −2.0 eV is a p-type material, andthe quinacridone derivative is included in one selected from the ilayer, the n layer, and a combination thereof, and the p-type materialis included in one selected from the p layer, the i layer, and acombination thereof.
 5. The photoelectric conversion device of claim 1,wherein the photoelectric conversion device includes a photodiode, asolar cell, an image sensing device, a photodetector, a photosensor, oran organic light emitting diode (OLED).
 6. The photoelectric conversiondevice of claim 1, wherein T¹ to T⁴ are one of same and different, andeach of T¹ to T⁴ are independently one of a cyano group (CN) and ahalogen, X¹ and X² are one of same and different, and each of X¹ and X²are independently one of oxygen (O) and sulfur (S), R¹ to R¹⁰ are one ofsame and different, and each of R¹ to R¹⁰ are independently one ofhydrogen, a substituted or unsubstituted C₁ to C₁₀ alkyl group, asubstituted or unsubstituted C₃ to C₁₀ cycloalkyl group, a cyano group(CN), and a halogen, wherein at least one of R¹ and R² is not hydrogen,w1 and w2 are each independently an integer of 0 or 1, k1 and k2 areeach independently an integer of 1 or 2, n1 and n2 are eachindependently an integer ranging from 0 to 3, m1 is an integer rangingfrom 1 to 3, and R¹¹ and R¹² are one of same and different, and each ofR¹¹ and R¹² are independently one of hydrogen, a substituted orunsubstituted C₁ to C₁₀ alkyl group, and a substituted or unsubstitutedC₃ to C₁₀ cycloalkyl group.
 7. The photoelectric conversion device ofclaim 1, wherein the quinacridone derivative includes one selected fromcompounds according to Chemical Formulas 2-7, 2-8 and a combinationthereof:


8. The photoelectric conversion device of claim 1, wherein thequinacridone derivative is represented by Chemical Formula 2-9:


9. The photoelectric conversion device of claim 1, wherein thequinacridone derivative has a LUMO (lowest unoccupied molecular orbital)level ranging from about −2.0 eV to about −5.0 eV.
 10. The photoelectricconversion device of claim 1, wherein the quinacridone derivative has abandgap ranging from about 1.5 eV to about 3.5 eV.
 11. The photoelectricconversion device of claim 1, wherein the quinacridone derivative has amaximum molar absorption coefficient of about 5.0×10² cm⁻¹·M⁻¹ to about1.0×10⁶ cm⁻¹·M⁻¹.
 12. A photoelectric conversion device, comprising: afirst electrode; a second electrode spaced apart from and configured toface the first electrode; and a photoactive layer between the firstelectrode and the second electrode, the photoactive layer including aquinacridone derivative represented by Chemical Formula 1:

wherein, in Chemical Formula 1, T¹ to T⁴ are one of same and different,and each of T¹ to T⁴ are independently one of a cyano group (CN), ahalogen, a substituted or unsubstituted C₆ to C₃₀ aryl group, and asubstituted or unsubstituted C₂ to C₃₀ heteroaryl group, X¹ and X² areone of same and different, and each of X¹ and X² are independently oneof oxygen (O), sulfur (S), and C(CN)₂, R¹ to R¹⁰ are one of same anddifferent, and each of R¹ to R¹⁰ are independently one of hydrogen, asubstituted or unsubstituted C₁ to C₃₀ alkyl group, a substituted orunsubstituted C₃ to C₃₀ cycloalkyl group, a cyano group (CN), a halogen,a substituted or unsubstituted C₆ to C₃₀ aryl group, and a substitutedor unsubstituted C₂ to C₃₀ heteroaryl group, w1 and w2 are eachindependently an integer ranging from 0 to 5, k1 and k2 are eachindependently an integer ranging from 1 to 4, n1 and n2 are eachindependently an integer ranging from 0 to 3, m1 is an integer rangingfrom 2 to 5, and R¹¹ and R¹² are one of same and different, and each ofR¹¹ and R¹² are independently one of hydrogen, a substituted orunsubstituted C₁ to C₃₀ alkyl group, and a substituted or unsubstitutedC₃ to C₃₀ cycloalkyl group.
 13. The photoelectric conversion device ofclaim 12, wherein T¹ to T⁴ are one of same and different, and each of T¹to T⁴ are independently one of a cyano group (CN) and a halogen, X¹ andX² are one of same and different, and each of X¹ and X² areindependently one of oxygen (O) and sulfur (S), R¹ to R¹⁰ are one ofsame and different, and each of R¹ to R¹⁰ are independently one ofhydrogen, a substituted or unsubstituted C₁ to C₁₀ alkyl group, asubstituted or unsubstituted C₃ to C₁₀ cycloalkyl group, a cyano group(CN), and a halogen, w1 and w2 are each independently an integer of 0 or1, k1 and k2 are each independently an integer of 1 or 2, n1 and n2 areeach independently an integer ranging from 0 to 3, m1 is an integerranging from 2 to 3, and R¹¹ and R¹² are one of same and different, andeach of R¹¹ and R¹² are independently one of hydrogen, a substituted orunsubstituted C₁ to C₁₀ alkyl group, and a substituted or unsubstitutedC₃ to C₁₀ cycloalkyl group.
 14. The photoelectric conversion device ofclaim 12, wherein the quinacridone derivative is represented by ChemicalFormula 2-10:


15. A photoelectric conversion device, comprising: a first electrode; asecond electrode spaced apart from and configured to face the firstelectrode; and a photoactive layer between the first electrode and thesecond electrode, the photoactive layer including a quinacridonederivative represented by Chemical Formula 1:

wherein, in Chemical Formula 1, T¹ to T⁴ are one of same and different,and each of T¹ to T⁴ are independently one of a cyano group (CN), ahalogen, a substituted or unsubstituted C₆ to C₃₀ aryl group, and asubstituted or unsubstituted C₂ to C₃₀ heteroaryl group, X¹ and X² areone of same and different, and each of X¹ and X² are independently oneof sulfur (S) and C(CN)₂, R¹ to R¹⁰ are one of same and different, andeach of R¹ to R¹⁰ are independently one of hydrogen, a substituted orunsubstituted C₁ to C₃₀ alkyl group, a substituted or unsubstituted C₃to C₃₀ cycloalkyl group, a cyano group (CN), a halogen, a substituted orunsubstituted C₆ to C₃₀ aryl group, and a substituted or unsubstitutedC₂ to C₃₀ heteroaryl group, w1 and w2 are each independently an integerranging from 0 to 5, k1 and k2 are each independently an integer rangingfrom 1 to 4, n1 and n2 are each independently an integer ranging from 0to 3, m1 is an integer ranging from 1 to 5, and R¹¹ and R¹² are one ofsame and different, and each of R¹¹ and R¹² are independently one ofhydrogen, a substituted or unsubstituted C₁ to C₃₀ alkyl group, and asubstituted or unsubstituted C₃ to C₃₀ cycloalkyl group.
 16. Thephotoelectric conversion device of claim 15, wherein T¹ to T⁴ are one ofsame and different, and each of T¹ to T⁴ are independently one of acyano group (CN) and a halogen, each of X¹ and X² are sulfur (S), R¹ toR¹⁰ are one of same and different, and each of R¹ to R¹⁰ areindependently one of hydrogen, a substituted or unsubstituted C₁ to C₁₀alkyl group, a substituted or unsubstituted C₃ to C₁₀ cycloalkyl group,a cyano group (CN), and a halogen, w1 and w2 are each independently aninteger of 0 or 1, k1 and k2 are each independently an integer of 1 or2, n1 and n2 are each independently an integer ranging from 0 to 3, m1is an integer ranging from 1 to 3, and R¹¹ and R¹² are one of same anddifferent, and each of R¹¹ and R¹² are independently one of hydrogen, asubstituted or unsubstituted C₁ to C₁₀ alkyl group, and a substituted orunsubstituted C₃ to C₁₀ cycloalkyl group.
 17. The photoelectricconversion device of claim 15, wherein the quinacridone derivativeincludes one selected from compounds according to Chemical Formulas 2-5,2-6 and a combination thereof:


18. A photoelectric conversion device, comprising: a first electrode; asecond electrode spaced apart from and configured to face the firstelectrode; and a photoactive layer between the first electrode and thesecond electrode, the photoactive layer including a quinacridonederivative represented by Chemical Formula 1:

wherein, in Chemical Formula 1, T¹ to T⁴ are one of same and different,and each of T¹ to T⁴ are independently one of a cyano group (CN), ahalogen, a substituted or unsubstituted C₆ to C₃₀ aryl group, and asubstituted or unsubstituted C₂ to C₃₀ heteroaryl group, X¹ and X² areone of same and different, and each of X¹ and X² are independently oneof oxygen, sulfur (S) and C(CN)₂, R¹ to R¹⁰ are one of same anddifferent, and each of R¹ to R¹⁰ are independently one of hydrogen, asubstituted or unsubstituted C₁ to C₃₀ alkyl group, a substituted orunsubstituted C₃ to C₃₀ cycloalkyl group, a cyano group (CN), a halogen,a substituted or unsubstituted C₆ to C₃₀ aryl group, and a substitutedor unsubstituted C₂ to C₃₀ heteroaryl group, w1 and w2 are eachindependently an integer ranging from 0 to 5, k1 and k2 are eachindependently an integer ranging from 1 to 4, n1 and n2 are eachindependently an integer ranging from 0 to 3, wherein at least one of n1and n2 is an integer ranging from 2 to 3, m1 is an integer ranging from1 to 5, and R¹¹ and R¹² are one of same and different, and each of R¹¹and R¹² are independently one of hydrogen, a substituted orunsubstituted C₁ to C₃₀ alkyl group, and a substituted or unsubstitutedC₃ to C₃₀ cycloalkyl group.
 19. The photoelectric conversion device ofclaim 18, wherein T¹ to T⁴ are one of same and different, and each of T¹to T⁴ are independently one of a cyano group (CN) and a halogen, X¹ andX² are one of same and different, and each of X¹ and X² areindependently one of oxygen (O) and sulfur (S), R¹ to R¹⁰ are one ofsame and different, and each of R¹ to R¹⁰ are independently one ofhydrogen, a substituted or unsubstituted C₁ to C₁₀ alkyl group, asubstituted or unsubstituted C₃ to C₁₀ cycloalkyl group, a cyano group(CN), and a halogen, w1 and w2 are each independently an integer of 0 or1, k1 and k2 are each independently an integer of 1 or 2, m1 is aninteger ranging from 1 to 3, and R¹¹ and R¹² are one of same anddifferent, and each of R¹¹ and R¹² are independently one of hydrogen, asubstituted or unsubstituted C₁ to C₁₀ alkyl group, and a substituted orunsubstituted C₃ to C₁₀ cycloalkyl group.
 20. The photoelectricconversion device of claim 18, wherein the quinacridone derivative isrepresented by Chemical Formula 2-4:


21. A photoelectric conversion device, comprising: a first electrode; asecond electrode spaced apart from and configured to face the firstelectrode; and a photoactive layer between the first electrode and thesecond electrode, the photoactive layer including a quinacridonederivative represented by Chemical Formula 1:

wherein, in Chemical Formula 1, T¹ to T⁴ are one of same and different,and each of T¹ to T⁴ are independently one of a halogen, a substitutedor unsubstituted C₆ to C₃₀ aryl group, and a substituted orunsubstituted C₂ to C₃₀ heteroaryl group, X¹ and X² are one of same anddifferent, and each of X¹ and X² are independently one of oxygen, sulfur(S) and C(CN)₂, R¹ to R¹⁰ are one of same and different, and each of R¹to R¹⁰ are independently one of hydrogen, a substituted or unsubstitutedC₁ to C₃₀ alkyl group, a substituted or unsubstituted C₃ to C₃₀cycloalkyl group, a cyano group (CN), a halogen, a substituted orunsubstituted C₆ to C₃₀ aryl group, and a substituted or unsubstitutedC₂ to C₃₀ heteroaryl group, w1 and w2 are each independently an integerranging from 0 to 5, k1 and k2 are each independently an integer rangingfrom 1 to 4, n1 and n2 are each independently an integer ranging from 0to 3, m1 is an integer ranging from 1 to 5, and R¹¹ and R¹² are one ofsame and different, and each of R¹¹ and R¹² are independently one ofhydrogen, a substituted or unsubstituted C₁ to C₃₀ alkyl group, and asubstituted or unsubstituted C₃ to C₃₀ cycloalkyl group.
 22. Thephotoelectric conversion device of claim 21, wherein each of T¹ to T⁴are a halogen, X¹ and X² are one of same and different, and each of X¹and X² are independently one of oxygen (O) and sulfur (S), R¹ to R¹⁰ areone of same and different, and each of R¹ to R¹⁰ are independently oneof hydrogen, a substituted or unsubstituted C₁ to C₁₀ alkyl group, asubstituted or unsubstituted C₃ to C₁₀ cycloalkyl group, a cyano group(CN), and a halogen, w1 and w2 are each independently an integer of 0 or1, k1 and k2 are each independently an integer of 1 or 2, n1 and n2 areeach independently an integer ranging from 0 to 3, wherein at least oneof n1 and n2 is an integer ranging from 2 to 3, m1 is an integer rangingfrom 1 to 3, and R¹¹ and R¹² are one of same and different, and each ofR¹¹ and R¹² are independently one of hydrogen, a substituted orunsubstituted C₁ to C₁₀ alkyl group, and a substituted or unsubstitutedC₃ to C₁₀ cycloalkyl group.
 23. The photoelectric conversion device ofclaim 21, wherein the quinacridone derivative is represented by ChemicalFormula 2-9:


24. A photoelectric conversion device, comprising: a first electrode; asecond electrode spaced apart from and configured to face the firstelectrode; and a photoactive layer between the first electrode and thesecond electrode, the photoactive layer including a quinacridonederivative represented by Chemical Formula 1:

wherein, in Chemical Formula 1, T¹ to T⁴ are one of same and different,and each of T¹ to T⁴ are independently one of a cyano group (CN), ahalogen, a substituted or unsubstituted C₆ to C₃₀ aryl group, and asubstituted or unsubstituted C₂ to C₃₀ heteroaryl group, X¹ and X² areone of same and different, and each of X¹ and X² are independently oneof oxygen, sulfur (S) and C(CN)₂, R¹ to R¹⁰ are one of same anddifferent, and each of R¹ to R¹⁰ are independently one of hydrogen, asubstituted or unsubstituted C₁ to C₃₀ alkyl group, a substituted orunsubstituted C₃ to C₃₀ cycloalkyl group, a cyano group (CN), a halogen,a substituted or unsubstituted C₆ to C₃₀ aryl group, and a substitutedor unsubstituted C₂ to C₃₀ heteroaryl group, w1 and w2 are eachindependently an integer ranging from 0 to 5, k1 and k2 are eachindependently an integer ranging from 1 to 4, n1 and n2 are eachindependently an integer ranging from 0 to 3, m1 is an integer rangingfrom 1 to 5, and R¹¹ and R¹² are one of same and different, and each ofR¹¹ and R¹² are independently one of a substituted or unsubstituted C₂to C₃₀ alkyl group, and a substituted or unsubstituted C₃ to C₃₀cycloalkyl group.
 25. The photoelectric conversion device of claim 24,wherein T¹ to T⁴ are one of same and different, and each of T¹ to T⁴ areindependently one of a cyano group (CN) and a halogen, X¹ and X² are oneof same and different, and each of X¹ and X² are independently one ofoxygen (O) and sulfur (S), R¹ to R¹⁰ are one of same and different, andeach of R¹ to R¹⁰ are independently one of hydrogen, a substituted orunsubstituted C₁ to C₁₀ alkyl group, a substituted or unsubstituted C₃to C₁₀ cycloalkyl group, a cyano group (CN), and a halogen, wherein atleast one of R¹ and R² is not a cyano group (CN), w1 and w2 are eachindependently an integer of 0 or 1, k1 and k2 are each independently aninteger of 1 or 2, n1 and n2 are each independently an integer rangingfrom 0 to 3, wherein at least one of n1 and n2 is an integer rangingfrom 2 to 3, m1 is an integer ranging from 1 to 3, and R¹¹ and R¹² areone of same and different, and each of R¹¹ and R¹² are independently oneof a substituted or unsubstituted C₂ to C₁₀ alkyl group, and asubstituted or unsubstituted C₃ to C₁₀ cycloalkyl group.
 26. Thephotoelectric conversion device of claim 24, wherein the quinacridonederivative is represented by Chemical Formula 2-3: